Seven
Aboard Nine destinations on the ballot. One honest read on each. One plan we would sail tomorrow.

The value play, and honestly the easiest on everyone's body. June in the Cascades is 70 degrees. Michael's family is a three-hour nonstop away; the rest of us fly six and a half hours nonstop to Seattle. Leavenworth is a Bavarian village on a river with a flat, shaded 4-mile loop at Icicle Gorge. Wallace Falls near Index has a gentle lower-falls walk. Olympia opens onto the Olympic Peninsula.

The catch is that it's Estes Park with a different mountain: two rental cars, three bases, grocery runs, and a couple of long drive days with a two-year-old in the back. We did that in September and it was great, but it was work. If anyone has family up there, tell us, because a home base changes this from good to excellent.

If the vote is "what's best for Noah," this wins. Beaches on Grace Bay is the only property we found with a real drop-off nursery for ages 0 to 2, plus a waterpark, Sesame Street characters, and a flat, calm beach the grandparents can walk. Florida flies there nonstop in under two hours. Everything is paid once, up front.

Two catches. It is the most expensive week on this list except Europe, roughly a third more than the cruise for the same nights. And San Diego to Providenciales is a ten-to-twelve-hour connection day each way. Worth advancing so the family can see the price side by side.

Everything good about the six-night applies here, with one more sea day. The problem is the calendar. Every Royal Caribbean sailing we found that pairs the Bahamas with Puerto Plata runs from Miami or Fort Lauderdale starting November 2027, not in May or June. Since Kelly's poll decides the time of year in a later round, this one is worth advancing only if the family is open to a fall or winter trip.

If we want seven nights in June from Fort Lauderdale, the real option is Odyssey of the Seas on a Western Caribbean loop (CocoCay, Falmouth, Grand Cayman), no Dominican Republic. Same driveway math as our pick, one extra night, a smaller and newer ship.

Nobody needs convincing that Kauai is beautiful. Two things hold it back for this trip specifically. First, the travel: the Florida four are looking at fourteen to sixteen hours each way through Honolulu and a six-hour time change, which is hard on a 74-year-old and cruel to a two-year-old's clock. Second, and this is new: Hurricane Lowell hit Kauai directly last week. The south shore around Poipu took the worst of it, and the state is telling visitors to postpone. Nine months is probably enough for rental houses to come back, but after Iniki in 1992 some of the resorts took years.

If the family is set on Hawaii, it should be a 2028 trip planned once the island has had a year, and probably from the north shore. Michael's family would have the easy version of this trip; ours would not.

This is Royal's "weekender" ship, brand new in 2024, and it only sails short trips out of Port Canaveral. Two things you should know before voting for it. It is not the easy one for Mom and Dad: Port Canaveral is a three-hour-plus drive from Pembroke Pines, not twenty-five minutes. And four nights is a short reward for Michael, Kelly and Noah crossing the country. If the family wants a short cruise, the six-night costs only a little more per night and puts the port in our backyard.

Same ship and port as the four-night, one night shorter, Friday to Monday. It's a wonderful trip for the four of us who live here and a rough trade for the three who don't. Better idea: keep this one in the back pocket as a Florida-only grandparents-and-Hailey weekend some other month.

We costed the two realistic shapes: a seven-night Mediterranean cruise from Barcelona or Rome, or a single villa for the week. Either way it lands around twenty to thirty thousand for seven, with a ten-hour overnight flight for Florida, thirteen-plus for San Diego, and a six-to-nine-hour time change. That is a lot to ask of Mom and Dad and a two-year-old for the same week we could do in our own time zone.

Hailey would get the most out of it of anyone, and she'd get even more at seventeen. Let's write it down as the trip after next, when Noah can carry his own backpack.

If anyone writes one in, here is what it's up against: no flight for four of us, one nonstop for the other three, a week that separates and reunites, real childcare for Noah, a doctor nearby, and around twelve thousand for all seven. The only write-in we found that clears most of that bar is a Disney Cruise Line trip from Port Canaveral: the nursery takes six months and up and Castaway Cay is the best private island in the business, but it costs about double Royal and the port is that same three-hour drive.